Beezus and Boxer Shorts: Inside the Minds of Two School-Aged Founders

In our Homework series, we explore the lives of ordinary kids with not-so-ordinary hobbies. Between school work and swimming lessons, these youngsters are also running successful businesses—(sometimes) with a bit of grown-up help.

Piper Williams didn’t like traditional girls’ underwear. She did like wearing her brother’s boxer shorts, but the fit wasn’t quite right. That’s when the four-and-a-half-year-old had an idea: boxer shorts for girls. With the help of her brother, mom, and dad, Piper’s idea bloomed into My Pipers, a business that keeps the whole family busy. Three years later, Piper and her brother, Tobin, leave a lot of the day-to-day up to Mom—they are, after all, in school—but they’re still in charge of design.

While the family is growing their boxer shorts business, Piper and Tobin also have busy lives reading books, making art, and tumbling on a gymnastics mat (in functional boxers, of course). Here, these two kid founders weigh in on everything from middle school to Simone Biles.

About Us

Tobin: I build Legos, I play video games, and I play soccer. Oh, and a little gymnastics.

What we’re watching and reading:

Piper: I’m watching a show called American Ninja Warrior, and I’m reading this book called Beezus and Ramona. They’re really fun.

Tobin: I’ve been watching Expedition Unknown. It’s about a guy named Josh Gates and he goes on these adventures and they’re trying to solve mysteries and stuff.

Our best adventure:

Tobin: I once went panning for gold. I didn’t get rich.

A typical week:

Piper: I go to school, and after I have gymnastics and homework. Then Tuesday, I have soccer. Wednesday, I have Hebrew school. Thursday, I have soccer. And Friday, I have gymnastics. Saturday, I have soccer games and gymnastics. Sunday... I don’t know.

How we started My Pipers:

Piper: I never liked to wear underwear because it was uncomfortable for me. One day, I tried on my brother’s boxer shorts under a dress. They were too long. But they worked. So we decided to make boxer shorts for girls, to fit under dresses and skirts. One of the designs has hearts and one of them says, “Free to be me.” They’re whatever we like to draw.

What our roles are in the business:

Piper: I draw the designs and I pick some colors. I do the logos, and I’m a model.

Tobin: Basically, I do almost all the drawings. We both take the orders to the mailbox.

How Mom helps us:

Tobin: Mom just finds the factories. She does a ton of the stuff. She picks out the cloth.

Piper: Well, she takes pictures on Instagram, some of the pictures of our products.

The best part of running a business is:

Piper: My favorite part is probably trying to design them, then wearing them.

The hardest part is:

Tobin: Probably traveling or going to the beach. Like, spending a few hours in the car to take just a few pictures for photoshoots.

Piper: I like all of it.

What our friends think of our business:

Tobin: Our friends don’t even know about it.

Piper: A lot of them think it’s really cool and we have teachers who have our hoodies. And a lot of our friends wear them.

Someone who inspires us:

Tobin: Probably my mom for always having all these really creative ideas, and they always turn out to be great ones.

Piper: I was going to say the same thing.

Something we’re proud of:

Piper: I’m proud that we made boxer shorts for girls, not just for boys.

Tobin: I’m proud of myself surviving school long enough to make it into middle school. Middle school’s way better than elementary school. Way, way, way, way better. First off, the teachers are actually nice. It’s definitely way more fun.

Our goals for the future are:

Piper: I would probably want to be an artist when I grow up. And I want to be an Olympic gymnast like Simone Biles.

Tobin: Well, I want to be an archeologist.

Advice we have for other young entrepreneurs is:

Piper: Just go for it!

Illustrations by João Fazenda

About the author

Dayna Winter

Dayna Winter is a Storyteller at Shopify, curious about the humans behind the brands and the moments that motivate them to create. She follows more dogs than humans on Instagram and isn't a real redhead.